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公开(公告)号：US06495700B1
公开(公告)日：2002-12-17
申请号：US10042586
申请日：2002-01-09
申请人： Joerg Bruening
发明人： Joerg Bruening
IPC分类号： C07D48704
CPC分类号： C07D487/04
摘要： A process for preparing phenserine compounds which are known acetylcholinesterase inhibitors from physostigmine compounds by hydrolysis to form an eseroline compound which is then condensed with an isocyanate.
摘要翻译： 通过水解制备从毒扁豆烷化合物得到的已知乙酰胆碱酯酶抑制剂以形成氰尿素化合物的苯丝氨酸化合物的方法，然后将其与异氰酸酯缩合。
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2.发明授权
公开(公告)号：US5886229A
公开(公告)日：1999-03-23
申请号：US87580
申请日：1998-05-29
IPC分类号： C07F5/02
CPC分类号： C07F5/027
摘要： Synthetic routes for forming alkali metal substituted borohydride compounds include the step of reacting an alkali metal reagent, a hydrogen donor, and a substituted borane. The reactions proceed without the requirement of specialized handling of alkali metal hydrides associated with prior synthetic processes for the production of alkali metal trisubstituted borohydride compounds. A chemical composition comprises solid potassium tri-sec-butyl borohydride.
摘要翻译： 用于形成碱金属取代的硼氢化合物的合成路线包括使碱金属试剂，氢供体和取代的硼烷反应的步骤。 反应进行而不需要专门处理与用于制备碱金属三取代硼氢化合物的先前合成方法相关的碱金属氢化物。 化学组成包括固体三仲丁基硼氢化钾。
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3.发明申请公开(公告)号：US20130267729A1
公开(公告)日：2013-10-10
申请号：US13824309
申请日：2011-09-23
申请人： Joerg Bruening
发明人： Joerg Bruening
IPC分类号： C07C231/02
CPC分类号： C07C231/02 , C07C231/12 , C07C231/14 , Y02P20/55 , C07C237/06 , C07C237/22
摘要： Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
摘要翻译： 公开了制备式1和1A化合物的方法。 第一种方法使用苄基氨基甲酸酯胺保护基团和式4的中间体。第二种方法使用氨基甲酸叔丁酯胺保护基团和式7的中间体。第三种方法利用二苄基胺保护基团。 还公开了化合物N- [2-氧代-2 - [（2,2,2-三氟乙基）氨基]乙基]氨基甲酸苯酯（式4的化合物）。 进一步公开的是从式15化合物和式1或1A化合物制备式14化合物的方法。
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公开(公告)号：US10202332B2
公开(公告)日：2019-02-12
申请号：US13824309
申请日：2011-09-23
申请人： Joerg Bruening
发明人： Joerg Bruening
IPC分类号： C07C261/00 , C07C231/02 , C07C231/12 , C07C231/14
摘要： Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
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5.发明授权Method of synthesis of lithium substituted borohydride reagents and method of synthesis of reactive lithium hydride 有权锂取代硼氢化物试剂的合成方法和反应性氢化锂的合成方法公开(公告)号：US06268537B1
公开(公告)日：2001-07-31
申请号：US09318415
申请日：1999-05-25
IPC分类号： C07F502
摘要： A synthetic route for forming lithium trisubstituted borohydride compounds comprises the step of reacting a processed lithium hydride reactant with a trisubstituted borane wherein the reaction is maintained for a period of time in a temperature range of approximately 15° C. to approximately 42° C. A method of synthesizing LiH comprises the step of reacting an alkyl lithium (for example, n-butyl lithium) with hydrogen in the presence of tetrahydrofuran. The reaction temperature is preferably maintained in the range of approximately −78° C. to approximately 25° C.
摘要翻译： 用于形成锂三取代硼氢化物化合物的合成路线包括将加工的氢化锂反应物与三取代的硼烷反应的步骤，其中反应在约15℃至约42℃的温度范围内保持一段时间。 合成LiH的方法包括在四氢呋喃存在下使烷基锂（例如正丁基锂）与氢反应的步骤。 反应温度优选保持在约-78℃至约25℃的范围内
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公开(公告)号：US08049029B2
公开(公告)日：2011-11-01
申请号：US12516807
申请日：2007-12-18
IPC分类号： C07C253/00
CPC分类号： C07C253/14 , C07C231/12 , C07C233/65 , C07C255/58
摘要： Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with a metal cyanide reagent, a copper(I) salt reagent, an iodide salt reagent and at least one compound of Formula 3 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; Y is Br or Cl; X is NR13 or O; n is 0 or 1; and R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and R1 is NHR3 comprising introducing a gas containing bromine into a liquid containing a compound of Formula 4, and further disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above.
摘要翻译： 公开了一种制备式1化合物的方法，包括使式2化合物与金属氰化物试剂，铜（I）盐试剂，碘化物盐试剂和至少一种式3化合物（其中R1是NHR3或OR4）接触 ; R2是CH3或Cl; R3是H，C1-C4烷基，环丙基，环丙基环丙基，环丙基甲基或甲基环丙基; R4是H或C1-C4烷基; Y为Br或Cl; X为NR 13或O; n为0或1; 并且R5，R6，R7，R8，R9，R10，R11，R12和R13如本公开所定义。 还公开了制备式2化合物的方法，其中Y是Br，R 1是NHR 3，包括将含溴的气体引入含有式4化合物的液体中，并且还公开了制备式5化合物的方法，其中 R14，R15，R16和Z如本公开中所定义，使用式1的化合物，其特征在于通过上述方法制备式1的化合物。
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公开(公告)号：US20100022780A1
公开(公告)日：2010-01-28
申请号：US12517429
申请日：2007-12-05
IPC分类号： C07D401/04 , C07C233/64 , C07D231/14
CPC分类号： C07C253/14 , C07D231/14 , C07D231/16 , C07D231/22 , C07D401/04 , C07C255/58
摘要： Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with at least one compound of Formula 3 in the presence of a solvent comprising one or more organic solvents selected from ethers and nitrites and a catalytically effective amount of a palladium complex comprising at least one tertiary phosphine ligand of Formula 4 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, alkyl, cyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; M1 is an alkali metal; and R5, R6 and R7 are defined in the disclosure; provided that when R2 is Cl, then X is Br. Also disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the aforedescribed method.
摘要翻译： 公开了一种制备式1化合物的方法，包括在包含一种或多种选自醚和亚硝酸盐的有机溶剂的溶剂存在下使式2的化合物与至少一种式3的化合物接触，并且催化有效量的 钯复合物，其包含至少一种式4的叔膦配体，其中R 1是NHR 3或OR 4; R2是CH3或Cl; R3是H，烷基，环丙基，环丙基甲基或甲基环丙基; R4是H或C1-C4烷基; M1是碱金属; 在本公开中定义了R5，R6和R7; 条件是当R2为Cl时，则X为Br。 还公开了制备式5化合物的方法，其中R14，R15，R16和Z如本公开内容所定义，使用式1的化合物，其特征在于通过上述方法制备式1的化合物。
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公开(公告)号：US06221331B1
公开(公告)日：2001-04-24
申请号：US09490982
申请日：2000-01-24
IPC分类号： C01B604
摘要： A synthetic route for forming lithium trisubstituted borohydride compounds comprises the step of reacting a processed lithium hydride reactant with a trisubstituted borane wherein the reaction is maintained for a period of time in a temperature range of approximately 15° C. to approximately 42° C. A method of synthesizing LiH comprises the step of reacting an alkyl lithium (for example, n-butyl lithium) with hydrogen in the presence of tetrahydrofuran. The reaction temperature is preferably maintained in the range of approximately −78° C. to approximately 25° C.
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公开(公告)号：US08748630B2
公开(公告)日：2014-06-10
申请号：US12517429
申请日：2007-12-05
IPC分类号： C07C253/14 , C07D231/14 , C07D231/16 , C07D231/22 , C07D401/04
CPC分类号： C07C253/14 , C07D231/14 , C07D231/16 , C07D231/22 , C07D401/04 , C07C255/58
摘要： Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with at least one compound of Formula 3 in the presence of a solvent comprising one or more organic solvents selected from ethers and nitriles and a catalytically effective amount of a palladium complex comprising at least one tertiary phosphine ligand of Formula 4 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, alkyl, cyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; M1 is an alkali metal; and R5, R6 and R7 are defined in the disclosure; provided that when R2 is Cl, then X is Br. Also disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the aforedescribed method.
摘要翻译： 公开了一种制备式1化合物的方法，包括使式2的化合物与至少一种式3的化合物在包含一种或多种选自醚和腈的有机溶剂的溶剂存在下接触，并且催化有效量的 钯复合物，其包含至少一种式4的叔膦配体，其中R 1是NHR 3或OR 4; R2是CH3或Cl; R3是H，烷基，环丙基，环丙基甲基或甲基环丙基; R4是H或C1-C4烷基; M1是碱金属; 在本公开中定义了R5，R6和R7; 条件是当R2为Cl时，则X为Br。 还公开了制备式5化合物的方法，其中R14，R15，R16和Z如本公开内容所定义，使用式1的化合物，其特征在于通过上述方法制备式1的化合物。
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公开(公告)号：US20100280251A1
公开(公告)日：2010-11-04
申请号：US12516807
申请日：2007-12-18
IPC分类号： C07D401/04 , C07C253/32 , C07C231/22 , C07D231/22 , C07D231/12
CPC分类号： C07C253/14 , C07C231/12 , C07C233/65 , C07C255/58
摘要： Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with a metal cyanide reagent, a copper(I) salt reagent, an iodide salt reagent and at least one compound of Formula 3 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; Y is Br or Cl; X is NR13 or O; n is 0 or 1; and R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure.Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and R1 is NHR3 comprising introducing a gas containing bromine into a liquid containing a compound of Formula 4, and further disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above.
摘要翻译： 公开了一种制备式1化合物的方法，包括使式2化合物与金属氰化物试剂，铜（I）盐试剂，碘化物盐试剂和至少一种式3化合物（其中R1是NHR3或OR4）接触 ; R2是CH3或Cl; R3是H，C1-C4烷基，环丙基，环丙基环丙基，环丙基甲基或甲基环丙基; R4是H或C1-C4烷基; Y为Br或Cl; X为NR 13或O; n为0或1; 并且R5，R6，R7，R8，R9，R10，R11，R12和R13如本公开所定义。 还公开了制备式2化合物的方法，其中Y是Br，R 1是NHR 3，包括将含溴的气体引入含有式4化合物的液体中，并且还公开了制备式5化合物的方法，其中 R14，R15，R16和Z如本公开中所定义，使用式1的化合物，其特征在于通过上述方法制备式1的化合物。
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